EP3409660B1 - Cycloaminderivat und pharmazeutische verwendung davon - Google Patents

Cycloaminderivat und pharmazeutische verwendung davon Download PDF

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EP3409660B1
EP3409660B1 EP17744386.8A EP17744386A EP3409660B1 EP 3409660 B1 EP3409660 B1 EP 3409660B1 EP 17744386 A EP17744386 A EP 17744386A EP 3409660 B1 EP3409660 B1 EP 3409660B1
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compound
atom
mmol
chloro
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EP3409660A4 (de
EP3409660A1 (de
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Shinnosuke Hayashi
Martial VALLET
Shinya YOKOSAKA
Kazuya OSUMI
Takumi Aoki
Hiroyuki Meguro
Mie Kaino
Kozue TAKAGAKI
Takehiro Takahashi
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Toray Industries Inc
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/451—Non condensed piperidines, e.g. piperocaine having a carbocyclic group directly attached to the heterocyclic ring, e.g. glutethimide, meperidine, loperamide, phencyclidine, piminodine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/4525—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with oxygen as a ring hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/06—Antipsoriatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/38—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
    • C07D211/96—Sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Claims (12)

  1. Cyclisches Aminderivat, dargestellt durch die folgende allgemeine Formel (I):
    Figure imgb0114
     wobei:
    R1 eine Alkyloxygruppe, die 1 bis 3 Kohlenstoffatome aufweist, darstellt, von denen 1 bis 3 Wasserstoffatome wahlweise durch ein oder mehrere Halogenatome substituiert sind;
    R2 ein Halogenatom darstellt;
    R3 ein Wasserstoffatom, ein Halogenatom oder eine Hydroxygruppe darstellt;
    R4 ein Wasserstoffatom oder ein Halogenatom darstellt;
    X für -C(=O)-(CH2)n-R5 oder -S(=O)2-R6 steht;
    n eine ganze Zahl von 0 bis 5 ist;
    R5 ein Wasserstoffatom, -OR7, -SR7, -S(=O)2-R7, -C(=O)-OR7,-N(R7)R8, eine Alkylgruppe mit 1 bis 3 Kohlenstoffatomen, von der 1 bis 3 Wasserstoffatome wahlweise durch ein oder mehrere Halogenatomen substituiert sind, oder eine Heteroarylgruppe, von der ein oder mehrere Wasserstoffatome wahlweise mit einer oder mehreren Alkylgruppen substituiert sind, die 1 bis 3 Kohlenstoffatomen aufweisen, darstellt;
    R6 eine Alkylgruppe, die 1 bis 5 Kohlenstoffatome aufweist, darstellt;
    R7 ein Wasserstoffatom oder eine Alkylgruppe, die 1 bis 3 Kohlenstoffatome aufweist, darstellt, von denen 1 bis 3 Wasserstoffatome wahlweise durch ein oder mehrere Halogenatome substituiert sind; und
    R8 ein Wasserstoffatom, eine Alkylgruppe, die 1 bis 3 Kohlenstoffatome aufweist, eine Acylgruppe, die 2 bis 4 Kohlenstoffatome aufweist, oder eine Alkylsulfonylgruppe, die 1 bis 3 Kohlenstoffatome aufweist, darstellt,
    oder ein pharmakologisch akzeptables Salz davon.
  2. Cyclisches Aminderivat nach Anspruch 1, wobei:
    R1 eine Alkyloxygruppe ist, die 1 bis 3 Kohlenstoffatome aufweist, von denen 1 bis 3 Wasserstoffatome wahlweise durch ein oder mehrere Fluoratome oder ein oder mehrere Chloratome substituiert sind;
    R2 ein Fluoratom oder ein Chloratom ist;
    R3 ein Wasserstoffatom, ein Fluoratom, ein Chloratom oder eine Hydroxygruppe ist;
    R4 ein Wasserstoffatom, ein Fluoratom oder ein Chloratom ist;
    R5 ein Wasserstoffatom, -OR7, -SR7, -S(=O)2-R7, -C(=O)-OR7 ist,-N(R7)R8, eine Alkylgruppe, die 1 bis 3 Kohlenstoffatome aufweist, von denen 1 bis 3 Wasserstoffatome wahlweise durch ein oder mehrere Fluoratome oder ein oder mehrere Chloratome substituiert sind, oder eine Heteroarylgruppe ist, von der ein oder mehrere Wasserstoffatome wahlweise durch eine oder mehrere Methylgruppen substituiert sind;
    R6 eine Alkylgruppe mit 1 bis 3 Kohlenstoffatomen ist; und
    R7 ein Wasserstoffatom oder eine Alkylgruppe mit 1 bis 3 Kohlenstoffatomen ist, von denen 1 bis 3 Wasserstoffatome wahlweise durch ein oder mehrere Fluoratome oder ein oder mehrere Chloratome substituiert sind,
    oder ein pharmakologisch akzeptables Salz davon.
  3. Cyclisches Aminderivat nach Anspruch 1, wobei:
    R1 eine Methoxygruppe ist, von der 1 bis 3 Wasserstoffatome wahlweise durch ein oder mehrere Fluoratome substituiert sind;
    R2 ein Fluoratom oder ein Chloratom ist;
    R3 ein Wasserstoffatom, ein Fluoratom oder eine Hydroxygruppe ist;
    R4 ein Wasserstoffatom oder ein Fluoratom ist;
    n eine ganze Zahl von 0 bis 4 ist;
    R5 ein Wasserstoffatom, -OR7, -N(R7)R8, eine Alkylgruppe, die 1 bis 3 Kohlenstoffatome aufweist, von denen 1 bis 3 Wasserstoffatome wahlweise durch ein oder mehrere Fluoratome substituiert sind, oder eine 5-gliedriger Ring Heteroarylgruppe ist, von der ein oder mehrere Wasserstoffatome wahlweise durch eine oder mehrere Methylgruppen substituiert sind;
    R6 eine Methylgruppe oder eine Ethylgruppe ist;
    R7 ein Wasserstoffatom oder eine Alkylgruppe ist, die1 bis 3 Kohlenstoffatome aufweist, von denen 1 bis 3 Wasserstoffatome wahlweise durch ein oder mehrere Fluoratome substituiert sind; und
    R8 ein Wasserstoffatom, eine Methylgruppe, eine Acylgruppe, die 2 bis 4 Kohlenstoffatome aufweist, oder eine Alkylsulfonylgruppe mit 1 bis 3 Kohlenstoffatomen ist,
    oder ein pharmakologisch akzeptables Salz davon.
  4. Cyclisches Aminderivat nach Anspruch 1, wobei:
    R1 eine Trifluormethoxygruppe ist;
    R2 ein Chloratom ist;
    R3 ein Wasserstoffatom ist;
    R4 ein Wasserstoffatom ist;
    X für -C(=O)-(CH2)n-R5 steht;
    n eine ganze Zahl von 0 bis 3 ist;
    R5 eine Methylgruppe, eine Trifluormethylgruppe, -N(R7)R8 oder eine Imidazolylgruppe, Triazolylgruppe oder Tetrazolylgruppe ist, wobei jedes Wasserstoffatom davon wahlweise durch eine oder mehrere Methylgruppen substituiert ist;
    R7 ein Wasserstoffatom, eine Methylgruppe oder eine Ethylgruppe ist; und
    R8 ein Wasserstoffatom, eine Methylgruppe, eine Acetylgruppe, eine Propionylgruppe, eine Methylsulfonylgruppe oder eine Ethylsulfonylgruppe ist,
    oder ein pharmakologisch akzeptables Salz davon.
  5. Cyklisches Aminderivat nach einem der Ansprüche 1 bis 4 oder ein pharmakologisch akzeptables Salz davon zur Verwendung als Arzneimittel.
  6. Arzneimittel, umfassend das cyclische Aminderivat nach einem der Ansprüche 1 bis 4 oder ein pharmakologisch akzeptables Salz davon als Wirkstoff.
  7. Cyclisches Aminderivat nach einem der Ansprüche 1 bis 4 oder ein pharmakologisch akzeptables Salz davon oder das Arzneimittel nach Anspruch 6 zur Verwendung bei der Behandlung oder zur Vorbeugung einer Autoimmunerkrankung.
  8. Cyclisches Aminderivat nach einem der Ansprüche 1 bis 4 oder ein pharmakologisch akzeptables Salz davon oder das Arzneimittel nach Anspruch 6 zur Verwendung bei der Behandlung oder zur Vorbeugung von Multipler Sklerose oder Psoriasis.
  9. Cyclisches Aminderivat nach einem der Ansprüche 1 bis 4 oder ein pharmakologisch akzeptables Salz davon oder das Arzneimittel nach Anspruch 6 zur Verwendung bei der Behandlung oder zur Vorbeugung einer allergischen Erkrankung.
  10. Cyclisches Aminderivat nach einem der Ansprüche 1 bis 4 oder ein pharmakologisch akzeptables Salz davon oder das Arzneimittel nach Anspruch 6 zur Verwendung bei der Behandlung oder zur Vorbeugung von allergischer Dermatitis.
  11. Cyclisches Aminderivat nach einem der Ansprüche 1 bis 4 oder ein pharmakologisch akzeptables Salz davon oder das Arzneimittel nach Anspruch 6 zur Verwendung bei der Behandlung oder zur Vorbeugung von Kontaktdermatitis oder atopischer Dermatitis.
  12. Retinoid-bezogener Orphan-Rezeptor y-Antagonist, umfassend das cyclische Aminderivat nach einem der Ansprüche 1 bis 4 oder ein pharmakologisch akzeptables Salz davon als Wirkstoff.
EP17744386.8A 2016-01-29 2017-01-27 Cycloaminderivat und pharmazeutische verwendung davon Active EP3409660B1 (de)

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BR112020013438A2 (pt) 2018-01-31 2020-12-01 Toray Industries, Inc. derivado de amina cíclico, medicamento, antagonista de receptor órfão gama relacionado a retinoide, e, agentes terapêuticos ou agentes preventivos para uma doença autoimune, para psoríase ou alopecia areata, para uma doença alérgica, para dermatite alérgica e para dermatite de contato ou dermatite atópica
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JPWO2017131156A1 (ja) 2018-11-22
PT3409660T (pt) 2020-07-31
US10364222B2 (en) 2019-07-30
PH12018501434A1 (en) 2019-03-04
EP3409660A4 (de) 2019-06-26
CN108473426B (zh) 2021-09-07
PL3409660T3 (pl) 2021-01-25
CA3009971A1 (en) 2017-08-03
MX2018008454A (es) 2018-08-14
IL260230B (en) 2020-06-30
SG11201805474PA (en) 2018-07-30
JP6807054B2 (ja) 2021-01-06
KR20180100573A (ko) 2018-09-11
MY195416A (en) 2023-01-20
TW201731816A (zh) 2017-09-16
CN108473426A (zh) 2018-08-31
ZA201804325B (en) 2019-09-25
HUE050744T2 (hu) 2021-01-28
US20180370916A1 (en) 2018-12-27
WO2017131156A1 (ja) 2017-08-03
RU2696862C1 (ru) 2019-08-07
AU2017210685A1 (en) 2018-07-05
ES2822606T3 (es) 2021-05-04
TR201912580U5 (tr) 2020-09-21
DK3409660T3 (da) 2020-08-31
BR112018015125A2 (pt) 2019-02-26
CA3009971C (en) 2024-03-19
AU2017210685B2 (en) 2020-09-24
TWI691486B (zh) 2020-04-21
EP3409660A1 (de) 2018-12-05
IL260230A (en) 2018-07-31

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